


The Things You Learn

by Chichi_10018



Category: Supernatural
Genre: Alternate Universe, High School, M/M
Language: English
Status: Completed
Published: 2014-03-15
Updated: 2014-03-15
Packaged: 2018-01-14 04:54:40
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 7,478
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1253620
Author URL: https://archiveofourown.org/users/Chichi_10018/pseuds/Chichi_10018
Summary: <blockquote class="userstuff">
              <p>The things that you learn about your best friend and what he can teach you! Cas told Dean an embarrassing fact about himself at a party during the weekend and now Dean wants to teach Cas how to have some quality time with himself!</p>
            </blockquote>





	The Things You Learn

**Author's Note:**

> This is an idea that a friend gave me to see if anyone would write it. I am taking a shot at it. I hope that I can make my second fic as good as I think that first one turned out to be!! Kudos and Comments are very highly appreciated!

High school officially sucked! Of course there are people that know that better than most. Castiel Novak knew that fact better than most people. Going to the party that Meg Master's had thrown over the past weekend had to been one of the stupidest mistakes that he had ever made in his short life. Stupid is not something that applies to Castiel very often. Of course you add Dean Winchester to the mix and there goes the straight A student with any choice of colleges, out the window. His best friend was not the sharpest tool in the shed but he managed to get by and was a great friend to Castiel. They had known each other for years. Castiel actually had come out to Dean that he was in fact gay. There was no hesitation to Dean's acceptance and from that moment on Castiel had a crush on his best friend.

"How is it that in all your life, Cas, you have never watched porn or masturbated?" Dean asked Castiel. Sitting on his bed next to his best friend, Castiel's face was bright red. 

"It is just something that is not important Dean. Not everyone here is someone that drips sexuality from his very pores. So what is so important about masturbating or watching porn?'' Cas said to a shocked Dean. Dean could not believe that his best friend had never felt the pleasure that comes from touching himself. 

"Come one Cas it is something that most guys learn to do when they are still younger than you are. I can't even believe that you don't know how to touch yourself." Dean says.

"Well Dean when you are learning what sex you actually are attracted to it is not something that crossed my mind. It is bad enough that you had to ask that question and now everyone at school knows that I am a freaking virgin." Cas growled at his friend.

Flashback

"Your turn Dean. Ask your question to anyone here!" Meg Masters told Dean. Dean looked around at the people sitting around the living room of Meg's parents’ house.

"Castiel have you ever slept with anyone?" Dean asked his best friend. Castiel just looks around at the group surrounding him waiting for his answer. Balthazar looked very curious at the answer, Gabriel just was smiling with a sucker in his mouth, Crowley looked bored, Jo was shooting daggers at Dean, Ash was just laughing his ass off, Sam looked at Dean horrified that he asked his friend that question, and Dean was just sitting there waiting for the answer. Castiel sat there stunned and blushes bright red.

"Well I take it that is a big fat no. Look at how red his face is getting. Clarence has never been laid. I bet that he has never had any type of experience including with himself." Meg states after Castiel doesn't answer. Castiel looks down and avoids participating in the activities the rest of the night. 

The group slowly dissipated after that embarrassing moment and Castiel just knew that it would be very short work from Balthazar, Meg, and Gabriel that everyone at school would know that he was still a virgin even though being a senior in high school.

"Dean why in the hell would you ask your best friend that question? You know that he is a private person and that is probably not his priority like you!" Sam Winchester admonished his brother as they left Meg's house. 

"It was an honest question Sammy. I thought that he had some experience at least." Dean told his brother. Castiel walked past Dean towards his own car.

"No Dean. To answer your question and to answer's Meg's. I have never slept with anyone and have never had any experience with even myself as she put it." Dean stops in shock as his friend kept walking and got into his own vehicle and left Dean staring at him. Sam just rolls his eyes and gets into the passenger seat of the Impala.

"Come on Dean. We have to get home. I think that you need to apologize to Cas when or if he decides to talk to you again." Sam calls out to Dean. Unfortunately he thinks that his bitch of a little brother is right as he gets into the driver’s seat and pulls away from Meg's.

End Flashback

"Look Cas I am sorry that I asked you that in front of everyone. I talked to everyone and they said that they wouldn't tell anyone. You just need to get some experience Cas! Come on it is something that is so easy and when you do it, it feels so amazing!" Dean told his friend.

Castiel just sits on the bed with his face burning. "I don't know what to even do Dean and I doubt that you are going to help me with this." Castiel tells Dean.

Looking at his friend Dean just says "Why wouldn't I help you Cas? You are my best friend and I embarrassed you in front of all our friends. Come on, get comfortable Cas it is time for you to learn about yourself." Castiel looks at his friend like he had grown another head. He had a major thing for his best friend and now here he was trying to get him to masturbate with him there. 

"No thanks Dean! I don't need to learn anything and I am not going to do it with you here." Castiel says shaking his head at Dean. Dean just smiles and tackles Castiel down on the bed. "What are you doing Dean?" Castiel asks breathlessly. 

"Come on Cas! I can explain things to you and let you try them out. I will go into the hallway and give you instructions if you don't want me in here with you." Dean says looking down at his blushing friend. Castiel just nods at Dean. "Great! Get comfortable and remove your clothing!" Dean says and gets up walking out into the hallway.

Castiel sits up and removes his t-shirt and moves his hands down to his sweatpants. Stopping there he looks out towards the hallway. "Dean I feel ridiculous doing this. Why is this so important to you anyway?" Castiel asks. Dean was really glad that he was out in the hallway when Castiel asked that question. Little did his best friend know, Dean actually felt more than friendship towards him. After Castiel came out to him Dean was shocked and super happy. He was in fact not as straight as he portrayed to the others around him. The only person that knew about him being bi was Sam and he would never tell anyone.

"It is important for people to have some type of experience like this Cas. Do you want to be a 40 year old virgin because you didn't know what to do when you meet someone you like?" Dean told Cas.

Castiel sat there and thought about what Dean had just said. He was going to be starting college not to long after graduation and if he did meet someone he wanted to know what to do. "I suppose not. What else do I need to do?" Cas said as he reached down and slid his sweatpants off himself.

"Well do you have like any lotion or lube maybe? It is going to make things go easier." Dean asks the younger teen.

"Why is that? I don't have anything in here like that. I believe that there is some lotion in the bathroom mirror." Castiel says looking around his room. 

"Hold on a minute. I will get it for you." Dean says moving down the hallway. Finding the lotion in the mirror, Dean walks back towards Castiel's room. "Cover up for a minute. I have the lotion for you." Dean says. He hears Castiel moving under the blankets on his bed. "Decent in there yet Cas?"

"Come on in Dean." Castiel yells over Dean's question. Dean walks into the room and has to stop for a minute. Cas is sitting up on the bed without his shirt on. The look that Cas is giving Dean is so freaking hot to Dean that he starts to sweat. "Dean are you okay?" Cas asks his friend when he stops and just stares at him. 

Clearing his throat, Dean walks over to Cas and tells him, "Yeah Cas sorry. Here is the lotion. It is going to make things easier by providing some lubrication so that you don't hurt yourself. If you don't have anything handy sometimes spit works but since this is the first time for you we are going to be cautious." 

Dean hands Castiel the bottle. "Okay if you say so Dean. Thanks for the information." Cas says staring at the bottle.

Dean turns away from Cas and makes his way out of the room. It is a good thing that he is going to be telling Cas what to do when he is out of the room. Just thinking about Cas being in that room listening to him give out directions on how to masturbate was causing Dean to get a bit warm under the collar. "What do I do now Dean?" Cas' voice shakes Dean out of his thoughts. 

"Still comfortable in there?" Dean asks.

"As comfortable as I can be I guess." Dean hears.

"Okay I want you to start to feel yourself before we get into the other things Cas. Just run your hands over yourself learning what feels good and what doesn't." Dean instructs. Cas looks out into the hallway knowing that Dean is just sitting there listening to him. It makes Cas feel warmer than he was before. Putting the lotion in reach on the bed, Cas then runs his hands down his chest towards his stomach.

"Am I supposed to feel anything besides ridiculous?" Cas inquires. 

"Give it a little bit Cas. You have just gotten started. Just run your hands over yourself and feel." Dean tells the other teen.

Cas runs his hands down his stomach leading to the trail of hair downwards. He felt ridiculous doing this when his best friend was in the hallway but it was Dean's idea. Moving his hands down towards his groin Cas' breath hitches and he inhales sharply.

"Everything okay in there?" Dean asks from the hall.

"Yeah just trying not to feel stupid doing this. I hate to ask this but isn't a person supposed to be hard to masturbate Dean?" Cas asks. Dean just groans softly and leans his head against the wall.

"Yes Cas you are. Try thinking of something that turns you on. There has to be something that makes you feel good to think about." Cas listens to Dean and turns red thinking about the few times that he was hard. All of those times involved thinking of Dean. Realizing that he was thinking of Dean out in the hallway listening to him, Cas finally notices that he is hard again. 

"Okay say that works. What do I do after that?" Cas asks.

"Take the lotion and pour a bit into your palm. If it is cold you might want to warm it up before you do anything. Having something cold touching your cock is not the best thing to have! After you are done warming it up take the lotion and spread it over your cock. The grip around the head and start to move your hand. Do what feels good to you." Dean says to Cas while trying not to groan at the thought that his friend is in the room doing what he told him to. 

Cas takes the lotion and does what Dean tells him. He thinks that it is really weird feeling but he is willing to try and knows that Dean is known for his experience around the school. Groaning at the feeling Cas starts to slowly move his hand. After about 5 minutes of this Cas starts to get frustrated. He feels the pleasure and the warmth pooling in his navel but there is something missing. Giving his cock another stroke Cas groans out loud.

"Everything okay in there? You doing what I told you Cas?" Dean asks.

"Yes Dean but nothing is going on. I am just getting frustrated. Maybe there is something wrong with me." Cas says stopping his motions. Dean peeks around the corner and sees his friend looking so frustrated and dejected that nothing was happening. Ducking back around the corner Dean thinks about what could be going on.

"Hey maybe that is what is missing Cas! Cover up again for a minute Cas." Dean shouts out.

Cas does this and tells Dean "Come on in. What do you think is missing Dean?"

"Well I think that you might need some visuals to go with trying. Let me find some good porn for you to watch while you do this." Dean tells Cas as he walks to Castiel's desk. Sitting at the computer, Dean searches for some appropriate porn for Cas. Knowing that his friend is gay he searches around for a few minutes before he finds something that might suit Cas. Finding something that looks promising Dean presses play and beats a hasty retreat back to the hallway. ''Okay Cas just watch that and go back to what I told you. Try varying the pressure of your hand around the head of your cock. See if that feels any better." He says sitting back down. 

Cas just looks at the screen of the computer and blushes a bright red. Why did he think that this was not going to work? Gripping his cock again he slowly moves his hand and varies the pressure as Dean told him. He can feel warmth pooling in him but after a while nothing happens. Pretty soon his arm is getting tired and he knows that Dean can't be comfortable out in the hallway.

"Dean come back in here and turn off that noise!" Cas yells to his friend laying back on the bed. Now normally Cas is a very bright person but add Dean to the mix and things slip his mind. What slipped his mind this time? He was completely naked on his bed! Dean slowly gets up from the floor waiting for the feeling to return to his legs. Listening to what was going on in the room was an experience that was different than what he was used to.

Moving back into the room had Dean staring at Cas. "Um Cas I think that you forgot something. Cover up before this gets any more awkward." Dean says turning bright red and turning his back on Cas. Cas looks down at himself, blushes red and dives under the covers. Clearing his throat Dean asks "Decent now Cas?"

"Yes you may turn that stuff off." He hears whispered. 

Moving to the computer and the loud porn noises that are coming from it, Dean just shakes his head and closes out the internet. Silence meets them as neither one knew what to say. After a few minutes of just listening to Cas breathe, Dean gets up and looks at his best friend. There are actual tears in his eyes. 

"Hey Cas come on it is alright. Don't worry about this not working out for you. I understand that this is something you are not comfortable with." Dean tries to reassure his friend.

"There has to be something wrong with me. I am a freak that doesn't know even how to masturbate properly. I will never be able to pleasure my boyfriend if I ever get one! I bet that you couldn't even get me to come once." Cas cries out.

Dean just sits next to his friend shocked at the last few words that he heard. Cas looks at Dean just as shocked at what he had just said. Peeking at Dean he realized that Dean didn't look disgusted at him. "Cas if you want me to help you do anything all you have to do is ask. You are my best friend and I would do anything for you." Dean told the teen next to him. To prove his point, Dean slides closer to Cas and cups his cheek.

"Dean, you don't have to do anything with me. I know that you are my best friend and I don't want to screw that up. Besides everyone knows that you are a ladies man." Cas says looking away from Dean. He is however shocked at the feeling of his best friend kissing him.

Pulling back from the kiss Dean tells Cas with nothing but honesty, "I am not as straight as everyone likes to think Cas. I have liked guys for a couple of years before I meet you. I was just not sure about it but there was something that eventually changed my mind. For you to come out and tell me made me so surprised and proud that you would confide that in me. In truth I think that the only guy that I have ever wanted to do things with is sitting right in front of me."

"What?" Cas breathes. 

"I have had a crush on you Cas. I just didn't know how to tell you. I think that maybe I asked you if you had slept with anyone at Meg's was to tell me if someone held your attention. Dean says to the shocked teen.

"Dean Winchester! Why didn't you say something sooner? I came out to you when we were freshman. I told you because you are my best friend and because you are the one that I have had feelings for since we were younger." Cas scolds Dean. Dean looks up at Cas and can't believe what he was hearing. All the years that could have been spent together were wasted. Well there was no time like the present to dive in he always believed.

"Cas would you be my boyfriend?" Dean asks shyly.

Cas just can't help the smile that spreads out on his face. "Of course I will Dean!"

Dean just smiles and pulls his now boyfriend over towards him. Looking at Dean was something that Cas would never get tired of doing but he wanted to get some experience and knowing that Dean wanted him made him warm all over.

"Dean, I hate to ask but is there anything that you can do about my problem?" Cas asks shyly. Chuckling at Cas' words Dean just leans in and kisses him.

"Of course we can Cas. It would be my pleasure to help you out." Dean breathes against Castiel's lips. Kissing Cas again he can feel the warmth radiating off him. Without breaking the kiss Dean takes off his over shirt and pushes Cas down so that they are lying on the bed. Never did he think that he would be able to kiss Cas much less teach him anything. Running his hands across Cas' shoulders and hearing a moan in response made Dean smile. Breaking the kiss to look down at Cas and seeing the look on his face was something to never forget. He was blushing sweetly and breathing heavier than he was a minute ago. "What do you want to do Cas? I can teach you anything that you want to learn."

"Please teach me everything Dean. I want to know that I am not some freak that can't have a normal experience with someone that they care for!" Cas whispered against Dean's lips. Dean’s eyes lit up at the thought that Cas wanted him to be the first person to have these moments with him. Leaning back down Dean seals their lips together and runs his tongue across Cas' lower lip asking to be let in. Cas eagerly lets him in and they explore each other's mouths. Cas runs his hands down Dean's back until he reaches the hem of the t-shirt in his way. Dean stops kissing Cas when he feels his shirt is being tugged up his torso. Raising himself up, Dean grabs the shirt and pulls it over his head. Cas can't do anything but stare at his boyfriend. Of course they had seen each other without clothes before but this was the first time that touching and looking was acceptable to each other. Slight brushes and looks in the past had been brushed off but now that was no longer the case. Reaching Dean's eyes, Cas was surprised to see a slight blush staining Dean's cheeks. 

"Why are you blushing Dean? You are gorgeous and I want to be able to look at my boyfriend." Cas asks. Dean just ducks his head down and kisses Cas again. Kissing him was something that could become his favorite thing, next to pie of course. Cas took this as his opportunity to take his fill of touching Dean where ever he could reach. Running his hands down Dean's shoulders and across his back, feeling all the warm skin that is getting warmer as he goes. Just being able to touch Dean is making Cas get hotter as he goes. Reaching down towards the front of Dean's jeans, Cas plays with the button asking Dean a silent question. Dean just smiles and nods his consent. Cas goes to work on the button and zipper of the jeans. Spreading the jeans open and seeing Dean's boxers made Cas moan. Dean smiles and stands up to remove the clothing. Sliding the jeans down his bow legs made Cas' mouth water. Dean is mostly muscle even if his diet is mostly fat. Seeing the tan skin being revealed to him, Cas just could not believe that it was true.

Dean kicks his jeans out of the way and sits back on the bed looking at Cas. Sitting there looking at him and realizing that he was now Cas' made his heart beat faster. Of course knowing that he was teaching Cas things that he didn't know about himself was something else that made his heart beat faster. It was going to be a major pleasure to teach Cas!

"Lay back Cas. I want to touch you and you can just feel right now. I believe that you are just trying to hard to please yourself. Maybe if someone else helps you it will not be too hard. You can always try this again alone to see if you can do it." Dean told Cas. Cas does as Dean tells him and just lays there waiting to see what Dean was going to do different than what he was doing. Dean reaches towards the blanket and slowly peels it away from Cas' torso. Slowly revealing the skin that he had made his mouth water. Castiel had perfect skin and even though he was skinny, he still had muscles. Leaning down towards Cas' chest, Dean slowly blows warm air over one of the nipples that was revealed. Cas squirms at the feeling even at the same time that his cock twitches under the rest of the blanket. Dean was laying just right to feel the twitch and smiles. After blowing some more air over the nipple he leans down and flicks his tongue over it. That causes Cas to moan and raise up off the bed. Dean just places his hand on Cas' stomach and pushes him back onto the bed. Running his tongue over the bud again and again until Dean feels he has spent enough time on one nipple, he moves to the other and continues the treatment to that one.

Cas is just laying there feeling what Dean is doing to his body and can't believe how hot he was. Never did he think that pleasure could be coursing through him at the touch of another. When he looks down at Dean and sees that he was waiting for eye contact, Dean moves the blanket down his body more. When the air hits his cock, Cas can't help but let out a whimper. Dean is just looking at his eyes not any where else on him. After he settles down, Dean then looks over his body. Seeing the blush that is slowly spreading down Dean's cheeks, Cas can feel the heat in his own at what his boyfriend is looking at. They knew everything about each other and now they were going to make something beautiful out of it.

Dean can't help the blush staining his cheeks. Cas might be small and nerdy but he was more than average downstairs. He was beautiful and Dean could not wait to prove it to him. Running his hands down Cas to let him know where he was heading, Dean slowly made his way towards the teens groin. Reaching his destination, Dean just took Cas' cock into his hand, feeling the shape and warmth of it. Cas moans and throws his head back against the pillows. Feeling the warmth that is spreading from his groin outward was something he would never forget. Just being there on the bed feeling what Dean was doing to him was a feeling that he could not describe. Dean was slowly moving his hand all over his cock using the lotion that Cas didn't wipe off. As Dean continued exploring his cock, Cas could feel the warmth in his stomach turn into a coil that was winding tighter and tighter. "Dean, I think that I am about to come." Cas moans at Dean.

"Just go with it Cas. Feel how amazing it is and just go with it." Dean whispered to his boyfriend. As he said those words the feeling in Cas' stomach slowly tightened just a little more until it exploded outward all through his body. Moaning and throwing his head back, Cas just comes all over himself and Dean. Stripe after stripe splatter's across his torso and Dean's hand that is still moving over his now softening cock. Dean just watches the pleasure that crosses Castiel's face, knowing that he caused it.

Smiling at Cas, Dean leans over him and kisses him, not caring that he is now laying in Castiel's come. "I told you that there was nothing wrong with you Cas. You can have an orgasm no problem. Just remember what this felt like so when you do this on your own you will have no problem." He says looking into Castiel's bright blue eyes. Cas just nods at the words Dean is saying. He is just over come with the pleasure that he felt go through him. "Little speechless there?" Dean asked. Nodding again caused Dean to chuckle. Getting up of Cas, Dean ran to the bathroom and got a warm wash cloth to clean Cas off with. Cas watched Dean and blushed at what the wash cloth was used for. He also was feeling bad. Dean was walking around with a tent in his boxers and all that Cas could do was watch and feel what was happening to him.

"Dean, what about you?" Cas asked. Dean just smiled and walked back over to the bed and crawled over Cas. Kissing Cas was very addicting to Dean as he did it again. Moaning into the kiss, Cas could feel the blood start to travel south again. Soon after Dean broke the kiss he was hard again. The beauty of being a teenager, Dean thought.

"Well since we are just starting out, maybe we should take things a little at a time." Dean replied. Cas just frowns and this and shakes his head. "What? I don't want to overwhelm you Cas."

"I asked you to teach me everything and we have wasted enough time Dean. We are going to be graduating soon and just got together. I want to know what it is like to give you pleasure too. Please can we keep going?" Cas asked scared that Dean was going to turn him down. Reaching under Cas' chin, Dean makes the other teen look at him and just nods yes. Cas gives him a smile that in a thousand years he will never forget. Cas then decides to move things along by running his hands down Dean, towards his boxers. Dean just lays back and lets Cas reach his destination. When Cas runs his fingers under the waist band, Dean lifts his hips off the bed to allow Cas to remove them if he wishes to. Cas puts his hands down Dean's boxers from the back and just moans at the feel of Dean's butt. Gathering his courage, Cas slowly moves them off of Dean's hips and slowly down the bow legs. Looking at Dean naked was something to behold. Cas felt beautiful when Dean looked at him so he hoped that Dean felt the same. Blushing lightly at the look on Cas' face, Dean just waits to see what Cas was going to do next.

He didn't have to wait long as Cas reached down and slowly wrapped his fingers around his cock. Dean just closes his eyes and moans at the feeling of Cas finally touching him. Hearing the lotion bottle opening up causes Dean to open his eyes. Cas was rubbing his hands together to warm the lotion. When he felt it was warm enough he replaced his hand on Dean. Moaning at the feeling, Dean just lets Cas explore. Running across a sensitive spot causes Dean to buck up into the hand on him. Cas takes his hand away afraid that he did something wrong. Dean looks at him and says "Keep going Cas. You just hit a very nice spot. You did nothing wrong. I would probably not have moaned if it hurt." Nodding and gaining some confidence that he was not going to do anything to hurt Dean, Cas resumes his exploration. Pretty soon Dean feels his orgasm approaching. "Cas you said you wanted me to teach you everything, right?" Dean asks.

"Yes Dean I do want to learn everything that you can teach me." Cas confirms for him. Dean reached down to Cas' hand and removes it. Cas arches an eyebrow at Dean. "What are you doing Dean? I was trying to bring you pleasure."

"You were bringing me pleasure Cas. Damn near too much. I want to make love to you before I come Cas." Dean replied.

Cas just blushes sweetly and leans down to capture Dean's lips in a kiss that was damn near sinful. Dean rolls them over so that he was over Cas again. Looking at the blush that was spreading across Cas the longer he looked, was something to see. Cas turned a lovely shade of pink and Dean loved to see it. "Do you want this Cas? We don't have to do anything that you don't feel comfortable doing yet." Dean asks Cas one last time. Cas just gives Dean a look that says he was not going to weasel out of teaching him everything. "Alright you don't have to pull a bitch face like Sam does Cas. I was just making sure that you wanted this." Dean chuckles. Cas relaxes back into the bed and just waits for Dean to get ready. Dean reaches down and positions Cas how he wanted him. 

Dean reaches over to the forgotten bottle of lotion and pours a healthy amount on to his palm. Running his fingers through it, making sure that they were covered by the slippery substance, Dean tells Cas, "I am going to prepare you now. Try to relax as much as possible and tell me if you are feeling any pain. I don't want to hurt you so I am going to take this slowly."

"I trust you completely Dean, you would never hurt me on purpose. I also know that I am not made out of glass so don't think that you are going to break me." Cas replies.

"Just relax and give it a bit. It will feel weird but when that passes it is amazing." Dean tells Cas going back to preparing him. Feeling that the first finger was moving with little resistance, Dean added more lotion to his other fingers and pushed a second one in along the first. Knowing the slight discomfort that Cas was feeling, Dean decided to find that spot that would make Cas see stars. Curling his finger's Dean knows when he has found it when Cas lets out a moan and clamps his hands over his mouth. "Feel good when I touch that?" Dean asks.

Cas removes his hands with a whimper as Dean continues to stroke his prostate. "It feels so good! Come on Dean I think that I am ready now!"

"Not yet Cas! I am going to do this properly or we will wait. Two finger's is nowhere enough to make room for me." Dean said sternly.

Cas just looks at Dean and nods that he was right. Smiling at his boyfriend, Dean adds more lotion again to his fingers and pushes in three in slowly. Reaching the rim, Dean twists his wrist to stretch Cas out as much as possible. When his finger's brush against Cas' prostate again, Cas almost screams at Dean. Feeling that he was met with almost no resistance, Dean removes his fingers. Whimpering at the loss of Dean's fingers, Cas looks at Dean, seeing him get off the bed to reach for his jeans. Getting into his wallet, Dean pulls out a condom and walks back to the bed. Opening the condom and applying it to himself, had Dean moaning. Reaching for the lotion bottle for the last time, Dean slather's his cover cock with the substance.

"Last time I will ask Cas, do you want to do this?" Dean asked the blushing teen beneath him. Looking into Dean's bright green eyes, Cas nods once and it was good enough for Dean. Reaching down, Dean guides his cock to Cas' entrance and slowly adds pressure to get inside. Dean could not help but moan at the feeling of Cas surrounding his cock. It was so tight and warm. Making past Cas' rim, Dean stopped moving so that Cas could get used to the feeling of something bigger than finger's breaching him. When Cas started squirming, Dean starts pushing in a few more inches.

"Dean please, move more! I will not break if you go faster." Cas panted out.

"I am going to take this slow Cas. I don't want to hurt you and if I do you might not want to do this again. I want to be able to make love to you as much as I can." Dean replies.

Moving forward again until he was bottomed in Cas, Dean holds still stalling his own orgasm. The pleasure running through him at being surrounded by Cas was almost too much. He had never believed that he was ever going to get the chance to tell Cas his feelings, much less get to be inside him. Leaning down to kiss Cas before he started moving caused Cas to just moan at the connection their lips and bodies were in. Breaking the kiss, Dean starts to withdraw from the heat causing Cas to whimper at the loss. That whimper was cut off as Dean moved back where he was with a slow thrust. Cas just can't hold back the moan at the feeling of Dean thrusting into him. He loved the feeling and wanted more.

Dean didn't disappoint him because he kept his motions of withdrawing and thrusting in and out of his body. After a few minutes, Dean changed the angle of penetration, brushing across Cas' prostate. Castiel arched up with a shout that rang out in the room. Moaning at the feeling of Cas tightening around his cock, Dean kept thrusting to hit that spot that made Cas see stars. Cas was speechless with pleasure running through him.

"Dean I think that I am getting close. Please please touch me!" Cas cried out.

"Right there with you Cas." Dean replied, reaching down to wrap his hand around Cas. When his hand made contact with Cas' cock, Cas let out another shout of pleasure. Dean starts to stroke in time with his thrusts that he is aiming at Cas' prostate with every thrust. Just when Dean thought that he was about to come, Cas let's out a moan and his cock starts shooting come over his chest and Dean's hand. Moaning at the tightening around him, Dean soon follows Cas into his own orgasm. Cas lets out another moan feeling Dean coming even through the condom. Dean keeps working Cas through his orgasm. After the teen goes limp with bliss, Dean lays down on top of him.

Laying on top of Cas waiting for feeling to come back to his blissed out body, Dean feels fingers running through his hair. Looking up all that he sees is blue eyes shining with love staring back at him. Smiling at Cas, Dean lifts up and reaches down to make sure the condom comes out he withdraws. Cas squirms at the feeling of his body closing up after Dean has withdrawn. Getting up off the bed, Dean ties the condom closed and throws it into the garbage next to the desk. Moving to the bathroom, Dean grabs a wash cloths and warms it to clean Cas off with.

When Dean gets back into the room he just chuckles lightly seeing that Cas was almost asleep. Moving to the bed, Dean leans down and whispers "Tired there angel?"

Cas opens his eyes and just smiles at Dean. Sitting on the bed, Dean lovingly runs the wash cloth over Cas' chest and cock. Knowing that this was going to make Cas squirm, Dean leans down between Cas' legs to check that no bleeding or tearing happened. On cue Cas started squirming when Dean's head was between his legs. Kissing his thigh to make Cas squirm once more results in a bitch face that Cas learned from Sam. Laughing out loud at Cas' face, Dean crawls over Cas to lay down next to him. Reaching his destination, Dean leans over and kisses the bitch face off of his face. Cas breaks the kiss and cuddles into Dean's bare chest.

"So do you want me to stay the night?" Dean asks his almost sleeping boyfriend.

"Don't ask stupid questions, Dean. My pillow should not be talking, just sleeping." Cas snarks and kisses Dean's chest. Dean just chuckles and closes his eyes after turning off the light next to the bed and covers them both up.

Next Morning

Cas feels warmth surrounding him as he slowly wakes up. Opening his eyes, Cas is met with the sight of Dean sleeping next to him. Looking at him and remembering the night that they had, made Cas blush. Looking down again, Cas lays back down next to Dean. Feeling the bed shift makes Dean open his beautiful eyes.

"Good morning beautiful." Dean yawns and leans down to kiss Cas. Even though Dean knows that he has terrible morning breath, Cas kisses back with enthusiasm. Breaking the kiss Dean asks Cas "Are you okay? I wasn't to rough last night was I?"

"I am fine Dean. Just need to take a shower and get something to eat. I think that I ended up skipping dinner last night." Cas replies. Crawling out of the warm blankets and making his way to his dresser to retrieve clothes, Cas glances back at Dean. Laughing at Dean's face staring at him, Cas asks "Are you just going to stay there or are you going to get in the shower with me?" Dean gets out of the bed and races to the bathroom behind Cas.

About a half and hour later, Cas and Dean emerge from the bathroom clean and wrapped in towels. Making their way to the bedroom to get dressed involved a lot of caresses and stolen kisses. After they were fully clothed, Cas and Dean decided to head out for breakfast at their favorite diner. Getting into the Impala and traveling to the local diner took less than 10 minutes. Making their way inside, Cas and Dean were surprised to see the group of friends all there. Cas blushed and tried to remove his hand from Dean's. Dean just gripped his fingers tighter and would not let go.

Sam was the first to notice the two and saw Cas' face. "Hey Cas, Dean pull up a seat." He told the pair that was just standing there. Dean moves first and to everyone's shock he kisses Cas' cheek. Meg just looked shocked, Balthazar was shooting dagger's at Gabriel, Gabriel just looked smug, Crowley was just watching the pair, Jo was smiling a huge smile, Ash was laughing his ass off, and Sam just smiled at Cas and offered him a seat next to him. Dean sat in the seat and pulled Cas onto his lap.

"What is the glare for Balthy? I take it that Gabriel won some bet between the two of you?" Dean asked the teen ignoring the looks of his friends who still were shocked at the turn of events. Cas just sits on Dean's lap and gets comfortable.

"The bloody bastard said that after you asked Cas if he was a virgin and he didn't answer that you were probably going to admit that you had feelings for him. He bet me that today you two would come in together and that Cas would finally have some experience under his belt." The British teen replied.

"So what did you lose to make you so pissed off that he was right?" Cas asks the question that is burning in everyone's minds. Of course Dean and Cas were burning bright red waiting for the answer.

"He has to buy my dessert for the rest of the school year. He is just being a sore loser. I just hope that he has saved some money because I love my dessert!" Gabriel says sticking a sucker in his mouth. The other teen just sticks his tongue out at Gabriel and everyone at the table laughs.

"So did everyone here know that we liked each other before we did?" Dean asks the group. All heads at the table nods yes. Dean and Cas are just shocked that it took them so long to realize that they wasted to much time. "Well why didn't any of you say anything?" Dean accuses the group. No one says anything for about a few minutes.

"Maybe you two needed to figure things out for yourselves. It might have taken you long enough but I think that because you two know each other so well that your relationship is going to last longer than others that are attracted to each other right off the bat." Sam told the shocked group.

"Figures that there would be a long winded explanation coming from just one person in this group and that it would be Sam." Crowley drawled out.

"Who cares that it has taken them so long to get together. I think that they are just to freaking cute and I am glad that they are happy." Jo pipes up.

Dean just looks at Jo with a smile and kisses Cas' cheek causing her to squeak in delight. "So Cas want to get something to eat? I am starving for some pie." Dean asks the teen on his lap. Nodding at Dean, Cas waves the waitress over and places an order of hamburgers, fries and a slice of pie for the two of them. After the rest of the group pays for their food they slowly dispersed to their respective homes. Dean moves Cas off his lap and keeps him close when their food arrives. They eat in silence for a few minutes until, Dean leans over and whispers in Cas' ear, "I love you Castiel Novak. I am sorry that it took so long for me to admit that I had feelings for you but I think that the bitch of a little brother of mine was right. I am glad that we are together and I hope that years down the road we can look back and remember our lives together."

Cas turns his head towards Dean and captures his lips in a kiss that was so loving and sensual. "I love you too, Dean Winchester. I hope for that too. Spending time with you has been one of the best things in my life and I am glad that no more time is going to be wasted with unrequited feelings. Hopefully one day when we are old we will look back at a life filled with love." Cas tells his boyfriend blushing. Linking their hands together again and kissing Cas' cheek Dean goes back to eating knowing that their lives together was just beginning.


End file.
